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Pronounced Catalytic Effect of a Micellar Solution of Sodium Dodecyl Sulfate (SDS) on the Efficient C‐S Bond Formation via an Odorless Thia‐Michael Addition Reaction through the in situ Generation of S ‐Alkylisothiouronium Salts
Author(s) -
Firouzabadi Habib,
Iranpoor Nasser,
Abbasi Mohammad
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800690
Subject(s) - chemistry , thiourea , sodium dodecyl sulfate , michael reaction , catalysis , thiol , micelle , organic chemistry , hydrolysis , adduct , micellar solutions , polymer chemistry , aqueous solution
A pronounced catalytic effect of sodium dodecyl sulfate (SDS) was observed on the in situ production of S ‐alkylisothiouronium salts via the reaction of primary, allyl and benzyl halides with thiourea in SDS droplets .Hydrolysis of the generated S ‐alkylisothiouronium salts in the palisade layer of the droplets produces the corresponding thiol moieties which are immediately added to the electron‐deficient olefins that are present in the micellar core to produce the thia‐Michael adducts. The entire route is an almost odorless process. The yields of the products are good to excellent and the method is applicable to large‐scale operation without any problem.